Hydroxyamine hydrochloride → HCID 135719043, compound

HRID 1006886Notes

Reaction equation

HRID 1006886 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl.[NH2:28][OH:29].C([O-])(=O)C.[Na+]>C(O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22](/[CH:25]=[N:28]\[OH:29])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22](/[CH:25]=[N:28]/[OH:29])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22502996HCID 22502996, compound

Product 2

HCID 135719043HCID 135719043, compoundHCID 136119044HCID 136119044, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Ethylpiperazin-1-yl)-3-(4-formylphenyl)isoquinoline (3.00 g) obtained in Example 17-5 was reacted with hydroxylamine hydrochloride (0.90 g) and sodium acetate (1.10 g) in ethanol (50 ml) at 60° C. for 2 hr. The reaction solution was evaporated, and then the resulting residue was extracted in methylene chloride, washed with brine and dried. The solvent was removed, and the resulting residue was isolated and purified by silica gel column chromatography (methylene chloride/methanol system), to give (Z)-1-(4-ethylpiperazin-1-yl)-3-(4-hydroxyiminomethylphenyl)isoquinoline (1.01 g) and (E)-1-(4-ethylpiperazin-1-yl)-3-(4-hydroxyiminomethylphenyl)isoquinoline (1.52 g), both as yellow solids. 0.30 g each of the compounds was converted into a hydrochloride in a conventional manner, to give the hydrochlorides of the title compounds as yellow powders (0.32 g and 0.35 g, respectively).

Workup

  1. customThe reaction solution was evaporated
  2. extractionthe resulting residue was extracted in methylene chloride
  3. washwashed with brine
  4. customdried
  5. customThe solvent was removed
  6. customthe resulting residue was isolated
  7. custompurified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-cac7b549524f49589a318a39aca9209b
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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